Today we’d like to introduce you to Maeghan Annen.
Hi Maeghan, we’d love for you to start by introducing yourself.
I never planned to be a small business owner, but the signs were always there. I remember creating little order forms at childhood cookouts so my brother and I could make and deliver s’mores to my dad’s friends. I was always wearing braided friendship bracelets and would beg my parents to take me to AC Moore for fuzzy posters and craft kits.
In 2020, I was planning a wedding and adjusting to life in a new city, a year into my first professional job and so excited about everything ahead. Like so many others, the pandemic shattered my world. I lost my job, canceled my wedding, and had to learn to sit still. My mental health plummeted and it took a while for me to start working my way out of that depression. Slowly, I started to notice the resurgence of grandma hobbies on social media and it took me back to my friendship bracelet days. I started to create again, but struggled with perfectionism and hated everything I made.
When I found machine embroidery, something clicked for me. It perfectly takes the creative, hands-on elements of crafting but combines it with a quality and consistency that makes me proud. In 2022, I used the annual bonus from my corporate job to buy a fifteen-year-old embroidery machine from Facebook Marketplace and spent my evenings learning how to digitize and embroider designs. That summer, I bought a pop-up canopy and a few wood crates, and setup to sell at a local sunflower festival. I only sold two t-shirts that day, but I was hooked. I went home, filed for a business license, and named the business after my cat since my own name, Maeghan, is tough to spell.
We all face challenges, but looking back would you describe it as a relatively smooth road?
The biggest struggles within my business have all been reflections of my own life. I overcommitted to markets because I couldn’t say no. I fell behind on orders because I struggled with priorities. I dealt with intense burnout because I never learned how to ask for help.
The best part about owning a small business is that I have full control. I’m able to adapt the business to my calendar and create products that I love. But the hardest part about owning a small business is that I have full control. Nothing can sell if I don’t make it. No one will find my product if I don’t market it.
When you own a small business, you are the brand, and that means your business and personal highs and lows are intertwined. For a long time, it felt like either my business could thrive or I could, but I’m slowly learning how to adjust my priorities so I’m able to show up for Penelope Annen Design as my best self, and I’m finding that the business has never been more fulfilling.
It is a constant balancing act to make sure I am taking care of myself, my household, my family, and also showing up as my best self at markets, keeping inventory stocked, releasing new designs, and shipping orders on time. I’ve failed at this over and over, and have had to learn how to forgive myself.
Can you tell our readers more about what you do and what you think sets you apart from others?
I embroider apparel with seasonal, local, and nature-inspired designs. I am a one-woman show and every single embroidered stitch comes from the spare bedroom of my Frederick County home. My brand is focused on cute and cozy clothing for everyday wear – your comfiest sweatshirt to curl up with a book or the hat that gets compliments every time you run out for coffee.
I’m incredibly proud of Penelope Annen’s growth, from a brand-new hobby that I just hoped could pay for itself, to a Limited Liability Company with sales that rival my full-time corporate income. I never expected this journey and find so much joy in being part of Maryland’s small business community.
The novelty has never worn off. Nothing beats the feeling of seeing a product I made with my own two hands out in the wild. Every Christmas I am humbled when I think about someone excited to find my product under their tree. I love getting to see my regulars at the same market every year and never for a moment take for granted that they are choosing to spend their hard-earned money on something I created.
Before we go, is there anything else you can share with us?
As we approach the holidays, it’s never been more important to shop small. Costs are going up all around us, but small businesses are working hard to keep our prices as low as possible because we know how it feels first-hand. Unlike big corporations, we’re feeling the same financial strain all households are experiencing, but we’re invested in our community and want to remain accessible to as many customers as we can. Studies consistently find that money spent with a small business is reinvested in the community at a far greater rate than with big corporations – plus nothing beats the kind of gift that says “I saw this and thought of you!”
You can find Penelope Annen Design in-person during three weekends this holiday season. The first weekend of November, Nov. 6-8, we will be at the Howard County Fairgrounds for the Howard County Crafts Spectacular. You can’t miss us – we’re the very first booth through the gates! Later in November, we’ll be set up at the Frederick Fairgrounds for The Maryland Christmas Show, Nov. 20-22 & 27-29. We will have tons of festive apparel for the holidays and plenty of giftable all-season designs, and we’ll be surrounded by hundreds of other incredible artists and small businesses.
Pricing:
- Pricing varies in-person vs online
- Embroidered Sweatshirts: $35-49
- Embroidered Tees: $29-36
- Embroidered Hats: $24 (available in-person only)
Contact Info:
- Website: https://penelopeannendesign.etsy.com
- Instagram: https://www.instagram.com/penelopeannen/







